2,6-anhydro-7-O-[2-acetamido-2-deoxy-6-O-methyl-4-O-phosphono-3-O-[(R)-3-(tetradecanoyloxy)tetradecyl]-β-D-glucopyranosyl]-3-deoxy-3-[(R)-3-(hydroxy)tetradecanamido]-4-O-[(R)-3-(hydroxy)tetradecyl]-D-glycero-D-ido-heptonic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-anhydro-7-O-[2-acetamido-2-deoxy-6-O-methyl-4-O-phosphono-3-O-[(R)-3-(tetradecanoyloxy)tetradecyl]-β-D-glucopyranosyl]-3-deoxy-3-[(R)-3-(hydroxy)tetradecanamido]-4-O-[(R)-3-(hydroxy)tetradecyl]-D-glycero-D-ido-heptonic acid
• 英文别名: 2,6-anhydro-7-O-[2-acetylamino-2-deoxy-6-O-methyl-4-O-phosphono-3-O-{(R)-3-tetradecanoyloxytetradecyl}-β-D-glucopyranosyl]-3-{(R)-3-hydroxytetradecanoylamino}-4-O-{(R)-3-hydroxytetradecyl}-3-deoxy-D-glycero-D-ido-heptonic acid；(2S,3R,4R,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3-acetamido-6-(methoxymethyl)-5-phosphonooxy-4-[(3R)-3-tetradecanoyloxytetradecoxy]oxan-2-yl]oxymethyl]-5-hydroxy-3-[[(3R)-3-hydroxytetradecanoyl]amino]-4-[(3R)-3-hydroxytetradecoxy]oxane-2-carboxylic acid
• 化学式: C₇₂H₁₃₇N₂O₁₉P
• 分子量: 1365.86
• InChiKey: GAFKZMSQTIARDG-XXFDJJJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.3
• 重原子数：
  94
• 可旋转键数：
  64
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  305
• 氢给体数：
  8
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  2,6-anhydro-7-O-[2-acetamido-2-deoxy-4-O-(diphenylphosphono)-6-O-methyl-3-O-[(R)-3-(tetradecanoyloxy)tetradecyl]-β-D-glucopyranosyl]-3-deoxy-3-[(R)-3-(hydroxy)tetradecanamido]-4-O-[(R)-3-(hydroxy)tetradecyl]-D-glycero-D-ido-heptonic acid 在 platinum(IV) oxide 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以96%的产率得到2,6-anhydro-7-O-[2-acetamido-2-deoxy-6-O-methyl-4-O-phosphono-3-O-[(R)-3-(tetradecanoyloxy)tetradecyl]-β-D-glucopyranosyl]-3-deoxy-3-[(R)-3-(hydroxy)tetradecanamido]-4-O-[(R)-3-(hydroxy)tetradecyl]-D-glycero-D-ido-heptonic acid
  参考文献：
  名称：

  具有醚链的脂质A型吡喃羧酸的合成及其生物学活性。

  摘要：

  描述了在C-3'和C-4位置均具有醚链的脂质A型吡喃羧酸的合成及其对人U937细胞的生物活性。

  DOI：

  10.1016/s0008-6215(01)00134-3

文献信息

• Ether type lipid a 1-carboxylic acid analogs
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20020161221A1

  公开（公告）日：2002-10-31

  A compound of formula (I) below, which exhibits excellent macrophage activity inhibitory action, is useful for the treatment or prophylaxis of inflammatory disorders, autoimmune diseases or septicemia. In a preferred embodiment, R 1 and R 3 each represents a C 1 -C 20 alkanoyl group which may optionally be substituted with one or more substituent groups selected from substituent group A, R 2 and R 4 each represents a C 1 -C 20 alkyl group which may optionally be substituted with one or more substituent groups selected from substituent group A, R 5 is a hydrogen atom, a halogen atom, a hydroxy group, or a C 1 -C 6 alkoxy group, and substituent group A is a halogen atom, a hydroxy group, an oxo group, a C 1 -C 20 alkoxy group, or a C 1 -C 20 alkanoyloxy group. 1

  以下为化合物式（I），该化合物表现出出色的巨噬细胞活性抑制作用，可用于治疗或预防炎症性疾病、自身免疫性疾病或败血症。在首选实施例中，R1和R3各代表一个C1-C20烷酰基团，该基团可以选择性地被一个或多个取代基团A所取代，R2和R4各代表一个C1-C20烷基团，该基团可以选择性地被一个或多个取代基团A所取代，R5是氢原子、卤素原子、羟基或C1-C6烷氧基团，取代基团A是卤素原子、羟基、氧代基、C1-C20烷氧基团或C1-C20烷酰氧基团。
• ETHER TYPE LIPID A1-CARBOXYLIC ACID ANALOGUES
  申请人：Sankyo Company, Limited

  公开号：EP1152007A1

  公开（公告）日：2001-11-07

  A compound of formula (I), which exhibits excellent macrophage activity inhibitory action, is useful for the treatment or prophylaxis of inflammatory disorders. autoimmune diseases or septicemia. R1 and R3 each represents a C1-C20 alkanoyl group which may optionally be substituted with one or more substituent groups selected from substituent group A, R2 and R4 each represents a C1-C20 alkyl group which may optionally be substituted with one or more substituent groups selected from substituent group A, R5 is a hydrogen atom, a halogen atom, a hydroxy group, or a C1-C6 alkoxy group, and Substituent group A is a halogen atom, a hydroxy group, an oxo group, a C1-C20 alkoxy group, or a C1-C20 alkanoyloxy group.

  式（I）化合物具有出色的巨噬细胞活性抑制作用，可用于治疗或预防炎症性疾病、自身免疫性疾病或败血症。 R1 和 R3 各自代表 C1-C20 烷酰基，可任选被一个或多个选自取代基 A 的取代基取代、 R2 和 R4 各自代表一个 C1-C20 烷基，可任选被一个或多个选自取代基 A 的取代基取代、 R5 是氢原子、卤素原子、羟基或 C1-C6 烷氧基，取代基 A 是卤素原子、羟基、氧代基团、C1-C20 烷氧基或 C1-C20 烷酰氧基。
• US6511965B2
  申请人：——

  公开号：US6511965B2

  公开（公告）日：2003-01-28
• Synthesis of lipid A type pyran carboxylic acids with ether chains and their biological activities
  作者：Yukiko Watanabe、Takashi Mochizuki、Masao Shiozaki、Saori Kanai、Shin-ichi Kurakata、Masahiro Nishijima

  DOI：10.1016/s0008-6215(01)00134-3

  日期：2001.7

  Synthesis of lipid A type pyran carboxylic acids having ether chains at both the C-3' and C-4 positions and their bioactivities toward human U937 cells are described.

  描述了在C-3'和C-4位置均具有醚链的脂质A型吡喃羧酸的合成及其对人U937细胞的生物活性。